Hydrochloric Acid → HCID 11641220, compound

HRID 2244014Notes

Reaction equation

HRID 2244014 reaction equation
C([O:3][C:4](=[O:36])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29](=[O:31])[CH3:30])=[C:25]([OH:32])[C:24]=3[CH2:33][CH2:34][CH3:35])=[CH:17][CH:16]=2)=[O:13])[CH:6]=1)C.O1CCCC1.[OH-].[Na+].Cl>O.CO>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][C:18]2[CH:19]=[CH:20][C:15]([NH:14][C:12](=[O:13])[NH:11][C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=3)[C:4]([OH:36])=[O:3])=[CH:16][CH:17]=2)=[C:24]([CH2:33][CH2:34][CH3:35])[C:25]=1[OH:32])(=[O:31])[CH3:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68431524HCID 68431524, compound

Product 1

HCID 11641220HCID 11641220, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To 3-{3-[4-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-ureido}-benzoic acid ethyl ester (200 mg, 0.40 mmol) in 1:1 tetrahydrofuran:methanol (10 mL) is added 2 N NaOH (5 mL). The reaction mixture is stirred vigorously at room temperature for 3 h. The reaction mixture is diluted with water (30 mL), acidified with 5N hydrochloric acid to pH=4, and extracted with ethyl acetate (3×70 mL). The combined organic extracts are washed with brine, dried over sodium sulfate, and concentrated to dryness. The resulting residue is purified by reverse phase HPLC using a gradient of 90:10 to 20:80 (H2O/0.1% TFA):CH3CN as eluent to give the title compound (24 mg, 12%). LC-MS (m/e): 461 (M−1); 1H NMR (DMSO-d6) δ 12.93 (1H, s), 12.85 (1 H, s), 8.93 (1 H, s), 8.77 (1 H, s), 8.15 (1H, s), 7.82 (1H, s), 7.30-7.60 (7 H, m), 6.75 (1H, d), 5.20 (2 H, s), 2.60 (5 H, m), 1.50 (2 H, m), 0.90 (3 H, t).

Workup

  1. extractionextracted with ethyl acetate (3×70 mL)
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customThe resulting residue is purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f7a31266c91f42d99fd4c68f839e6a2d
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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